Month: June 2021

Reference of 92525-10-5, The chemical industry reduces the impact on the environment during synthesis 92525-10-5, name is 3-Iodo-1-methyl-1H-pyrazole, I believe this compound will play a more active role in future production and life.

Step 1-Synthesis of 2-(1-methyl-1H-pyrazol-3-yl)-4-(trimethylsilyl)but-3-yn-2-ol To a solution of 3-iodo-1-methyl-1H-pyrazole (378 mg, 1.82 mmol) in dry DCM (15 mL) at 0 C. under an atmosphere of nitrogen, was introduced ethylmagnesium bromide (2.0 mL of a 1.0M solution in THF, 2.0 mmol). After 30 minutes at 0 C., the reaction mixture was warmed to RT for 15 minutes, then introduced to a solution of 4-(trimethylsilyl)but-3-yn-2-one (0.37 ml, 2.18 mmol) in dry DCM (5 ml) at 0 C. under an atmosphere of nitrogen. The reaction mixture was warmed to RT for 16 hr. Following addition of saturated aqueous ammonium chloride (5 ml), the reaction mixture was extracted with DCM (3*5 mL extractions). The combined organic extracts were dried (Na2SO4), filtered and concentrated in vacuo. Purification of the residue by silica gel flash column chromatography (heptane/EtOAc gradient) furnished the title compound as an orange-brown oil: 1H NMR (500 MHz, CDCl3) delta 0.15 (9H, d, J=3.5 Hz), 1.82 (3H, s), 3.18 (1H, s), 3.86 (3H, s), 6.28 (1H, d, J=2.2 Hz), 7.26 (1H, d, J=2.2 Hz); LC-MS: m/z=+222.95 (M+H)+.

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, 3-Iodo-1-methyl-1H-pyrazole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Genentech, Inc.; US2012/214762; (2012); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Related Products of 876343-24-7, The chemical industry reduces the impact on the environment during synthesis 876343-24-7, name is 1-Ethyl-1H-pyrazol-4-amine, I believe this compound will play a more active role in future production and life.

Example 1; iV-(l-ethyl-lJ-pyrazol-4-yl)-2-[2-methoxy-4-(l,6-naphthyridin-4-yloxy)phenyl]acetamide; Diisopropylethylamine (0.417 ml) and 2-(7-azabenzotriazol-l-yl)- 1,1,3,3-tetramethyluronium hexafluorophosphate(V) (0.395 g) were added in turn to a stirred mixture of 2-[2-methoxy-4-(l,6-naphthyridin-4-yloxy)phenyl]acetic acid (0.27 g),4-amino-l -ethyl- 1/i-pyrazole (0.179 g) and DMF (3 ml) and the resultant mixture was stirred at ambient temperature for 18 hours. The resultant mixture was evaporated and the residue was purified by reversed-phase preparative HPLC on a Waters ‘Xbridge’ Cl 8 column (5 microns silica, 19 mm diameter, 100 mm length) using a solvent gradient comprising 13:17 to 100:0 mixtures of acetonitrile and 0.02M aqueous ammonium carbonate as eluent for 4.5 minutes at a flow rate of 40 ml per minute. The material so obtained was further purified by column chromatography on silica using a solvent gradient from methylene chloride to a 9:1 mixture of methylene chloride and 7M methanolic ammonia solution as eluent. There was thus obtained the title compound as a solid (0.12 g); 1H NMR Spectrum: (DMSOd6) 1.33 (t, 3H), 3.61 (s, 2H), 3.77 (s, 3H), 4.07 (q, 2H), 6.75 (d, IH), 6.91 (m, IH), 7.06 (d, IH), 7.37 (d, IH), 7.42 (s, IH), 7.88 (s, IH), 7.92 (d, IH), 8.82 (d, IH), 8.9 (d, IH), 9.71 (s, IH), 10.05 (s, IH); Mass Spectrum: M+H+404.

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, 1-Ethyl-1H-pyrazol-4-amine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2007/113565; (2007); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 2075-45-8 as follows. name: 4-Bromo-1H-pyrazole

Step 1 : 4-(Methylthio)-1H-pyrazole A suspension of 4-bromopyrazole (4 g, 27 mmol) in tetrahydrofuran (68 mL) was cooled to 0C and n-butyllithium (2.5 M in hexanes, 35.9 mL, 90 mmol) was added dropwise over a period of 20 min. The reaction mixture was stirred at room temperature for 1 h and then was cooled to 0C. 1 ,2-Dimethyldisulfide (2.66 mL, 30.0 mmol) was added dropwise. The reaction mixture was stirred at 0C for 1.5 h. The reaction mixture was poured into water (150 mL) and then it was acidified to pH~8 with a saturated aqueous solution of ammonium chloride and a solution of aqueous hydrochloric acid (1 N). The mixture was extracted with ethyl acetate (150 mL x 3) and the combined organic layers were dried over sodium sulfate, filtered and concentrated under reduced pressure to afford 4-(methylthio)-1 H-pyrazole (3300 mg). 1H NMR (500 MHz, CDCI3) delta 2.36 (s, 3H), 7.63 (s, 2H).

According to the analysis of related databases, 2075-45-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; PFIZER INC.; AHN, Kay; BOEHM, Markus; CABRAL, Shawn; CARPINO, Philip A.; FUTATSUGI, Kentaro; HEPWORTH, David; KUNG, Daniel W.; ORR, Suvi; WANG, Jian; WO2013/150416; (2013); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 51516-70-2 as follows. Recommanded Product: 51516-70-2

General procedure: To a stirred solution of the intermediate compounds 1a-1d (1 mmol) and triethylamine (2 mmol) in DMF (12 mL) medium, a mixture of EDCI (1 mmol) and HOBt (1mmol) was added and the reaction mixture was stirred at room temperature for 30 min, then a mixture of compounds 2a-2d (1 mmol) and DMF (5 mL) was added, the reaction was stirred at room temperature. And the reaction progress was monitored by TLC. After completion of the reaction, the product was added into chloroform, then extracted from chloroform with water, and washed successively with 0.2 mol/L hydrochloric acid, water,2 mol/L sodium hydroxide, water, saturated sodium chloride, then dried, concentrated and purified by preparative thin layer chromatography (PE:EA = 8:1) followed by recrystallization from ethanol.

According to the analysis of related databases, 51516-70-2, the application of this compound in the production field has become more and more popular.

Reference:
Article; Xiao, Jin-Jing; Liao, Min; Chu, Ming-Jie; Ren, Zi-Li; Zhang, Xin; Lv, Xian-Hai; Cao, Hai-Qun; Molecules; vol. 20; 1; (2015); p. 807 – 821;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

These common heterocyclic compound, 1621-91-6, name is 1H-Pyrazole-3-carboxylic acid, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route. Formula: C4H4N2O2

Dimethyl sulfate (236 g, 177 mL, 1.87 mol) was added dropwise over 45 min to a stirred solution of pyrazole-3-carboxylic acid (200 g, 1.78 mol) in 20% aqueous sodium hydroxide (850 mL) at 40 C. The reaction mixture was heated at 80 C for 2 h, cooled to room temperature, filtered, the filtrate acidified to pH 1 with concentrated HCI, the precipitate filtered, washed with water, and dried under vacuum to yield 1-methylpyrazole-5-carboxylic acid (85 g, 38%). The filtrate was concentrated in vacuo to 800 ML, extracted with chloroform (15X400 mL), the organic phase dried over anhydrous magnesium sulfate, concentrated in vacuo, and the residue recrystallized from isopropanol to yield 1-METHYLPYRAZOLE-3-CARBOXYLIC acid (74 g) as a white crystalline solid.

The synthetic route of 1H-Pyrazole-3-carboxylic acid has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK & CO., INC.; WO2004/58702; (2004); A2;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 25711-30-2, name is 1,5-Dimethyl-1H-pyrazole-4-carbaldehyde, belongs to pyrazoles-derivatives compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 25711-30-2, Formula: C6H8N2O

Example 17 N4-[(trans-4-{[(1,5-dimethyl-1H-pyrazol-4-yl)methyl]amino}cyclohexyl)methyl]-5-nitro-N2-[2-(trifluoromethoxy)benzyl]pyrimidine-2,4-diamine A mixture of N4-[(trans-4-aminocyclohexyl)methyl]-5-nitro-N2-[2-(trifluoromethoxy)benzyl]-pyrimidine-2,4-diamine (100 mg, 0.23 mmol) and 1,5-dimethyl-1H-pyrazole-4-carbaldehyde (23 mg, 0.19 mmol) in CH2Cl2 (15 mL) was stirred at room temperature for 1 h. NaBH(OAc)3 (200 mg, 0.95 mmol) was then added to the reaction mixture and stirred for another 16 h. The reaction mixture was diluted with 1M Na2CO3 to pH 9-10 and the organic phase was separated. The aqueous phase was extracted with CH2Cl2. The combined organic phase was dried over Na2SO4 and concentrated. The resulting residue was purified by silica gel prep TLC using 98:2 CH2Cl2:MeOH as an eluent to afford 54 mg (52%) of the title compound as a pale yellow foam, m/z 549.7 [M+1]+

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, 1,5-Dimethyl-1H-pyrazole-4-carbaldehyde, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Boehringer Ingelheim Pharmaceuticals, Inc.; US2006/25433; (2006); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 120068-79-3, name is 5-Amino-1-(2,6-dichloro-4-(trifluoromethyl)phenyl)-1H-pyrazole-3-carbonitrile, belongs to pyrazoles-derivatives compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 120068-79-3, Quality Control of 5-Amino-1-(2,6-dichloro-4-(trifluoromethyl)phenyl)-1H-pyrazole-3-carbonitrile

EXAMPLE 6 Use of Trifluoromethanesulfinic Acid Prepared in Accordance with the Invention for Synthesis of Fipronil A 500 ml jacketed reactor with stirrer, baffles and condenser was initially charged under a nitrogen atmosphere with 103 g of ethylbenzene, 6.3 g of dimethylisopropylamine hydrochloride (0.050 mol, 99%) and 15.5 g of potassium chloride (0.208 mmol). Subsequently, 31.5 g of trifluoromethanesulfinic acid (0.223 mol, 95.0%), 17.9 g of dimethylisopropylamine (0.203 mol, 99%) and 24.2 g of thionyl chloride (203 mmol, 99.7%) were metered in at 0 C. with cooling. After subsequently adding 54.8 g of 5-amino-3-cyano-1-(2,6-dichlor-4-trifluoromethylphenyl)pyrazole, the reaction mixture was stirred at 0 C. for 1 h, then heated to 35 C. over 45 min and stirred at 35 C. for a further 10 h. After the reaction had been quenched with sodium hydroxide solution and extracted with ethyl acetate and ethylbenzene, a nonisolated yield of fipronil of 80% was obtained in the crude solution (determination by means of quantitative HPLC).

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, 5-Amino-1-(2,6-dichloro-4-(trifluoromethyl)phenyl)-1H-pyrazole-3-carbonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BASF SE; US2011/190510; (2011); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Synthetic Route of 155377-19-8,Some common heterocyclic compound, 155377-19-8, name is Ethyl 3-(trifluoromethyl)pyrazole-4-carboxylate, molecular formula is C7H7F3N2O2, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

To a solution of ethyl 3- {trifluoromethyl) -lH-pyrazole-4- carboxylate (0.208 g, 1.0 mmol) in DMF were added lH-indol-5- ylboronic acid (0.322 g, 2.00 mmol), Cu(OAc)2 (0.136 g, 0.75 rninol)/ and pyridine (0.162 ml, 2.00 mmol) and the mixture was stirred at room temperature for 3 days . The mixture was diluted with DCM and filtered through a pad of silica gel. The filtrate was concentrated in vacuo and the residue was purified by silica gel column chromatography (3:1 hexanes/EtOAc) to give ethyl 1- (lH-indol-5-yl) -3- (trifluoromethyl) -lH-pyrazole-4- carboxylate (0.313 g, 97%) as a solid: 1H NMR (CDCl3) delta 1.39 (t, 3H7 J = 7.0 Hz), 4.37 Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; WO2008/11131; (2008); A2;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Electric Literature of 139756-02-8, A common heterocyclic compound, 139756-02-8, name is 4-Amino-1-methyl-3-N-propyl-1H-pyrazole-5-carboxamide, molecular formula is C8H14N4O, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

Synthesis of Bb; Step 7: 4-amino-i -methyl-3 -propyl- 1 H-pyrazole-5-carboxamide (1 eq) and 3 -Nitrobenzaldehyde (1.1 eq ) were suspended in methanol 5 ml and the mixtureheated at 65 C for 1.5 hours after conformation of forming of imine by TLC. Added CuC12 (3 eq) and the reaction mixture heated at7O C under 02 for 2.5 hours. After completion of the reaction, the methanol was removed under vacuum. Then workup with ethyl acetate and water. Separate the organic layer and Water layer re-extracted with 2×25 ml ethyl acetate. The combined organic layers are washed with brinesolution, concentrated under vacuum. The residue was purified by columnchromatography on silica the desired product Bb as a brown solid; yield 85%. ?H NMR(400 MHz DMSO): 8.90 (s 1H), .8.49(m iH), 8.35(m 1H), 7.84-7.80 (m 2H) 4.24(s3H), 2.8(t J = 7.3Hz 2H), 1 .80(m 2H), 0.95(t J = 7.3 Hz 3H). MASS: ESI [M + H] :314.12; Elemental anal. caled. for C15H15N503 C, 57.50; H, 4.83; N, 22.35; 0, 15.32;found C, 57.40; H, 4.85; N, 22.38; 0, 15.37

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; COUNCIL OF SCIENTIFIC AND INDUSTRIAL RESEARCH; SAWANT, Sanghapal Damodar; GINNEREDDY, Lakshma Reddy; MAHESUNI, Srinivas; SYED, Sajad Hussain; DAR, Mohd Ishaq; NARGOTRA, Amit; MAHAJAN, Priya; VISHWAKARMA, Ram Asrey; WO2015/114647; (2015); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 78703-53-4, name is 1,3-Dimethyl-1H-pyrazole-4-carboxylic acid, A new synthetic method of this compound is introduced below., COA of Formula: C6H8N2O2

To a solution of 10b (578.8 g, 4.13 mol) in DMAC (2.0 L) at 0 C was added thionyl chloride (514.7 g, 4.33 mol) dropwise, maintaining the temperature below 15 C. After addition of DMAC (0.25 L), the mixture was stirred at 0-15 C for 0.5 h. To this mixture was added 8 (500.0 g, 3.93 mol) portionwise, maintaining the temperature below 40 C. After addition of DMAC (0.75 L), the mixture was stirred at 15-40 C for 1 h. Then, H2O (1.0 L), NaOH (346.1 g, 8.65 mol) in H2O (4.5 L), and H2O (3.5 L) were successively added dropwise at 15-40 C. The resulting slurry was stirred for 2 h, and then filtered. Wet solids were washed with H2O (1.5 L) and dried in vacuo at 50 C to give the title compound 13b (923 g, 94%) as a pale brown solid; mp 188-189 C; 1H NMR (500 MHz, DMSO-d6) delta 2.19 (s, 3H), 3.98 (s, 3H), 6.62 (ddd, 4JHF=3.3 Hz, J=8.5, 3.3 Hz, 1H), 6.83 (s, 1H), 7.02 (dd, 4JHF=6.5 Hz, J=3.0 Hz, 1H), 7.07 (dd, 3JHF=10.0 Hz, J=9.0 Hz, 1H), 9.48 (br s, 1H), 9.85 (s, 1H); 13C NMR (125 MHz, DMSO-d6) delta 13.0, 38.5, 107.5, 112.9, 112.9, 115.8 (2JCF=21.3 Hz), 125.0 (2JCF=12.5 Hz), 135.2, 145.4, 149.0 (1JCF=235.0 Hz), 153.3 (3JCF=1.3 Hz), 158.0; IR (ATR) 3229, 1651, 1625, 1547, 1531, 1504, 1452, 1377, 1303, 1274, 1260, 1226, 1178, 1109, 1056, 1024, 973, 893, 850, 817, 804, 788, 771, 746, 678, 638, 624, 595, 527, 510, 461, 451, 432, 422, 412 cm-1; Anal. Calcd for C12H12N3O2F: C, 57.83; H, 4.85; N, 16.86. Found: C, 57.62; H, 4.69; N, 16.88.

The synthetic route of 78703-53-4 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Ishimoto, Kazuhisa; Sawai, Yasuhiro; Fukuda, Naohiro; Nagata, Toshiaki; Ikemoto, Tomomi; Tetrahedron; vol. 69; 40; (2013); p. 8564 – 8571;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics